We bought a house this winter that had a rather expensive looking landscape design going on. The back of the house abuts a road, and is sloped downward rather steeply. Looking at the neighbor, I can see the retaining wall was once stacked rocks and dirt. Their side looks decently stable. There is a wooden fence running across the top of this (level dirt and a sidewalk on the other side).

We have a section of the fence that is leaning a bit. I thought originally we'd have to repair it and set new concrete, but turns out it's easy to push back in place, concrete and post look good, but the ground is not stable on our side. We did some research and decided planting to stabilze the earth was our best choice. I bought some blueberry plants, and have plans to add strawberries. Went out to dig into the the beds today and discovered they are actually very shallow. For whatever reason (cost?) the landscaper left the heavy clay soil, put down weed fabric, then filled in about two inches of dirt.

I am really not sure how to approach this....do I pull up the weed fabric, dig out the front of the bad soil and fill with good stuff, then plant? Will that destabilize the fence? Give up and just do strawberries? Weirdly, there are two bushes already growing there (I think also blueberries?), but I have no idea how they managed to get them planted deep enough!

I would get the weed fabric out first. The stuff is horrible for soil and plants. You can reuse the soil that is on top. Just move it to the side, pull up the fabric, and put it back. Then add some compost and dig it into the top 8-10 inches of soil (don't do this when the ground is soaking wet). Organic matter, such as compost, will help improve your clay soil.

From your picture, it's hard to tell how much room there is between the fence and the wood retaining wall. If it's around 4 feet, I would improve the soil in the front 3 feet or so and plant there. I wouldn't loosen the soil near the fence posts. In fact, you may want to tamp down around your posts before starting to work in the area. I'm wondering if the fence installer didn't bury the posts deep enough. I've never had fence posts lean unless they were rotting off.

I think it's closer to three feet to the fence. It definitely looks like the fence post wasn't sunk in deep enough. Should we try to set it in more concrete? Or just hope the extra soil will do the job?

Ugh, we had that fabric all over our yard, which is now a bunch of raised beds. SUCH a pain.

We've had similar fence issues. My guess is that, if the posts were driven deep enough in the first place, then they are now rotting. If that is the case, you can either replace them, wrap the base of the new ones to prevent this, and then put some concrete and then soil in. That's how we did our new ones.

If you keep these, I would use concrete. If the posts are rotting, soil will just make that continue.

Absolutely do not put concrete around wood posts. Wood shrinks as it ages. Concrete expands at different rates than wood. By putting concrete around a wooden post, you are basically creating a giant water cup for your wood post to sit in which facilitates rot and makes it much more difficult to replace when the time comes. Wooden posts last much longer if packed with clay and/or treated with chemicals to inhibit wood rot.

To the OP, I would fix your fence first before dealing with the planting bed issues. Nothing worse than replacing a fence while trampling over a bunch of freshly done landscaping.